Calgary, Canada

With over 1.3 million residents, Calgary is a booming oil and gas hub, but don't let the high salaries and corporate glitz fool you - this prairie city has its fair share of bureaucratic headaches and weather-related woes. The tax burden is heavy, and the Chinook winds can wreak havoc on everything from landscaping to infrastructure, as evidenced by the recent catastrophic failures of the city's main water feeder main. Still, Calgary's economy remains one of the strongest in Canada, and its affordable housing and burgeoning arts scene make it an attractive option for those who can brave the bureaucratic red tape and unpredictable climate.